Herbicide

ABSTRACT

A new and valuable mixture of an aniline derivative and an oxadiazolidinedione or an oxadiazinedione or an ester of cyanoacrylic acid or a biscarbamate, which mixture has a good herbicidal action, and a process for controlling the growth of unwanted plants with these compounds.

United States Patent 11 1 1111 3,877,924

Fischer 51 Apr. 15, 1975 HERBICIDE [56] References Cited [75] Inventor: Adolf Fischer, Mutterstadt, UNITED STATES PATENTS Germany 3,257,190 6/1966 Soper 71/105 Assigneec Badische Anilin- & S0da Fabrik Zschocke et al Aktiengesellschaft,

L d i h f /Rh i Germany Primary ExaminerJames 0. Thomas, Jr.

Att ,A t, F Jh t ,K'1,Th Filed: Oct. 1970 & ggrlilizleffgen or zrm 0 ns on e1 ompson [21] Appl. No.: 78,244

[57] ABSTRACT Foreign Application Priority Data A new and valuable mixture of an aniline derivative Oct. 8, 1969 Germany 1950601 and an oxadiazolidinedione or an oxadiazinedione or an ester of cyanoacrylic acid or a biscarbamate, which [52] US. Cl. 71/92; 71/103; 71/104; mixture has a good herbicidal action, and a process 71/105; 71/111; 71/115; 71/118; 71/121 for controlling the growth of unwanted plants with [51] Int. Cl AOln 9/22 these compounds. [58] Field of Search 71/92, 121, 111, 104, 105 10 Claims, N0 Drawings HERBICIDE The present invention relates to herbicides. particularly selective herbicides. which are suitable for controlling unwanted plants. especially without damaging crop plants.

It is known to use dinitroaniline derivatives. oxadiazine derivatives, oxadiazolidinedione derivatives. cyanoacrylic acid ethyl ester compounds and diurethane compounds as herbicidal active ingredients; however. their action is not always satisfactory.

l have now found that herbicides containing a mixture of a. a compound having the formula where R denotes m-chlorophenyl. m-trifluoromethylphenyl. 3.4-dichlorophenyl. 3-chloro-4-bromophenyl, methylphenyl or 3-chloro-4-methylphenyl and R denotes 3-isopropylcarbamoyloxyphenyl. m-carboxyisopropylphenyl. 3.4-dichlorophenyl. 4-chlorophenyl. phenyl. 3-trifluoromethylphenyl. 3-butylcarbamoyloxyphenyl. cyclohexyl. m-ethylcarbamoyloxyphenyl or mtert-butylcarbamoyloxyphenyl. or

c. a compound having the formula where X and Y are identical or different and each denotes hydrogen. fluoro or trifluoromethyl. or

d. a compound having the formula i where X and Y denote nitrile. acetyl or COOR". R"

denoting a lower aliphatic radical. R denotes hydrogen. a lower aliphatic radical or aralkyl. R denotes halogen. a lower saturated or unsaturated aliphatic radical. haloalkyl. alkoxy. cyano or thiocyano. non-esterified or esterified carboxyl. nitro. non-N-alkylated or N-alkylated sulfonamide or acylated amino, and n denotes one of the integers 0. l. 2, 3, 4 and 5, or

e. a compound having the formula where R denotes haloalkyl. have a good herbicidal action on broadleaved and grassy weeds. including panic grass species.

The individual active ingredients may be mixed in any desired ratio. Mixtures are. however. preferred whose weight ratio of a to b or c or cl or e is from 5:1 to 1:3.

The herbicides according to the invention may be used as solutions. emulsions, suspensions or dusts. The form of application depends entirely on the purpose for which the agents are being used; in any case it should ensure a fine distribution of the active ingredient.

For the preparation of solutions to be sprayed direct. the solution in water is suitable. However. hydrocarbons. such as tetrahydronaphthalene. and alkylated naphthalenes may also be used as spray liquids.

Aqueous formulations may be prepared from emulsion concentrates. pastes or wettable powders by adding water. To prepare emulsions the ingredients as such or dissolved in a solvent may be homogenized in water or organic solvents by means of wetting or dispersing agents. Concentrates which are suitable for dilution with water may be prepared from active ingredient. emulsifying or dispersing agent and possibly solvent.

Dusts may be prepared by mixing or grinding the active ingredients with a solid carrier.

The action of the mixtures according to the invention is illustrated by the following examples.

EXAMPLE 1 An agricultural plot is sown with seeds of Gussypium herbaceum, Glycine liispida. Ecliinoclzloa crus-galli. Lolium mulrlflormn, Pou unnua. Sinapis arvensix, Matri- (aria chamomillu and Galinsoga parviflora. The soil prepared in this manner is then treated with the following amounts of the individual active ingredients and mixtures thereof. each amount of each active ingredient and each mixture being dispersed in 500 liters of water per hectare:

-Continued 1 4-trifluoromethyl-2.6-dinitro-N.N-dipropylanilinc. 1.5 and 3 VI 2-( 3,4-dichlnrophcn)'l )-4-mcthyl-l.lJ-oxadiazolidinc-3.5- kg P hccwrc v dione. 1 and 3 kg per hcclurc; ll 4-tnfluoromcthyl-Z.fi-dmltro-N-B-chlorocthyl-N-allylamlmc. V11 4-(3.4-dichlorophcnyl)-2-mcthyl-1.2.-1-oxadiazolidinc-3.5- and 3 kg p hectare:

dionc, 1 and 3 k per h mr Ill N -propylJfLB-chloroethyl-4-trlfluoromcthyl-2.6- Vlll 2-(m-lcrl-bulylcarhumnyloxyphgny])-4 mcthy| 2 4 dmitroanillnc. 1.5 and 3 kg per hectare:

oxadiazolidine-3.5-dionc. 0.5 and 2 k Y er h tar E p LL L 3.5-dionc. 1.5 and 3 kg per hectare:

l+\' :1.5+().5k "1 11+ V1 2 l Z-methyL-H3-trifluoromcthylphcnyl)-tetrahydro-l.14- III \H 3 1 k per hectare; oxadiazinc-35-dronc. 1.5 and 3 kg per hectare: l\' VIII 3 [,5 ()5 k per hectare \'l ethyl-[34N-phcnyl-N-mcthyl)-ammo-a-cyanoacrylatc. 1.5

and 3 kg per hectare: 1+ 1V 1.5 1.5 kg per hectare; After 4 weeks it is ascertained that the mixtures. 10 V I 15 kg P hccwrcl 111+ VI 1.5 1.5 kg per hectare:

compared with the individual active ingredients, have an excellent herbicidal action combined with very good crop plant compatibility.

The resuits f the experiment are given in the follow After 3 to 4 weeks it is ascertained that the mixtures,

ing table; 15 compared with the individual active ingredients, have 1 11 111 l\' \'l \'ll \'lll kg/hal 1.5 2 2 3 Z 3 1.5 2 (1.5 2 1 3 1 3 (1.5 2

(i0.r.\' \'piun| lu'rlnu'i'mn U 5 (l (l (l (I (1 U 30 0 (l (l l0 l0 (ilvcim' llixpillu i) 5 U U (l (l O (l (1 30 (l (l 0 15 U 50 Iic/iinuchlim c'rux-gnlli 8O 90 85 95 90 100 80 80 3O 60 (1 41) (l 55 90 Lnlillln mulllllurum 8U 90 X5 95 90 100 81) 85 5O 70 4U 5U 4U 6U 6U 90 Pm! umiml 9U 95 90 l()() 95 N10 85 9O 6O 8U 5U 7U 45 55 65 90 Sinuplx urvvnxix (l (l 3O 2O 31) U U 80 95 90 100 80 90 100 100 .llu/rir'uriu clmmumillu l) (l 10 0 U U (1 80 9O 90 9O 80 90 I00 100 (iulinmgu pnrrifluru 20 35 0 (l 85 100 90 100 80 95 100 100 l+\' ll+V| lll+V1l l\'+\lll l.5+().5 2+1 2+1 l.5+().5

(iuxsypinni lu'rhuu'um U 0 0 10 Glycine liixpirlu 0 (l 0 lz't'liinmlllml rrm-gulli 100 85 90 l()() Lulimn llmliifluruln 100 100 100 100 Pm! unnml 100 100 I00 100 Sinupix arrunsis 8(1 100 1011 100 Malrit'al'iu c/ummmillu 80 100 80 100 (inlinxugu [)lll'llifltlftl 100 100 100 100 U no damage 100 complete destruction X MPLE 2 a stronger herbicidal action combined with more favor- An agricultural plot 15 sown wlth seeds of Gossypium ab e Crop plant compdtlblmy lierbacemn, Glycine lzispizla, Ec/zinoc/zluu crus-galli, 40 The results of the eXPerimem are given in the fOllOW- Lolium multlflurum, Poa annua, Amaranllms retrog table:

1 II III l\' V VI kg/ha 1.5 3 1.5 3 1.5 3 1.5 3 1.5 3 1.5 3

G0.v.r \'pimn ln'rhaceum (l (l O 0 0 (l 0 O 0 Glycine ltispizlu O 10 0 1) O (1 0 l() 0 l0 5 20 Ecliinuclilou vrus-gulli 8O 9O 80 95 80 100 40 40 40 8O Lulium mulrifluruni 8O 95 8O 95 80 100 60 80 60 80 65 85 Pan annua 90 100 85 100 80 l()() 85 7O 85 70 90 Anmrumlzus lvlmflm'm' 5 0 10 0 3O 95 9O 8O 80 Gulinsogu purwfluru 20 3O 20 55 5 35 85 95 8O 9O 100 Sinupis urrensis 0 l0 10 40 5 30 80 9O 8O 90 8O 80 l+l\ ll+\" lll+Vl kg/ha 1.5+1 1.5+1.5 1.5-+1.5

Gosxypimn lu'rlmwum l) 0 Glycine liixpirlu O 5 Echinucliluu crux-gulli 1(10 1()() 100 Lulinni lnullifluruln 101) 100 100 Pm! unnuu 100 l()() 100 Gulinsugu purri/lum 100 100 Sinupix urrunxis 80 90 85 (1 no damage complete destruction flexus, Galinsoga part-[flora and Sinapis arrensis. The EXAMPLE 3 soil prepared in this manner is then treated with the following amounts of the individual active ingredients and An agricultural plot is sown with seeds of G0ss \'pium mixture thereof, each amount of each active ingredient 65 lzerbaceum, Glycine hispida, Ec/zinoclzloa crus-galli, and each mixture being dispersed in 500 liters Of ater Lolium multiflorum, Poa annua, Manic-aria chamoper hectare: milla, Galinsoga part-[flora and Amarant/zus retruflexus.

N-(1,1-dimethyl-2-ch1oroethyl)-carbamic acid-( mcarbomethoxyaminophenyl )-ester; N-(2,Z-dimethyl-Z-chloroethyl)-carbamic acid-(mcarbomethoxyaminophenyl )-ester;

-[tris-(chloromethyl)-methy1l-carbamic acid-( mcarbomethoxyaminophenyl)-ester. 1 claim: 1. A herbicide composition containing a herbicidally effective amount of a mixture of a. a compound having the formula wherein R is trifluoromethyl and R is nitro, R is propyl or B-chloroethyl and R is propyl or allyl. and

b. a compound selected from the group consisting of 2-( m-isopropylcarbamoyloxyphenyl )-4-methy1- l.2,4-oxadia2olidine-3.S-dione and 2-( 3,4- dichlorophenyl)-4-methyl-1.2.4-oxadiazolidine- 3.5-dione in a weight ratio of tub in the range of :1 to 1:3.

2. A herbicide composition as claimed in claim 1 wherein compound a is a member selected from the group consisting of 4-trifluoromethyl-2.o-dinitro-N.N- dipropylaniline. 4-trifluoromethyl-2.o-dinitro-N-fichloroethyl-N-allylaniline, and N-propyl-N-B- chloroethyl-4-trifluoromethyl-2.o-dinitroaniline.

3. A herbicide composition containing a herbicidally effective amount of a mixture of the compounds at. 4-trifluoromethyl-2,o-dinitro-N.N-dipropylaniline or N-propyl-N-B-chloroethyl-4-trifluoromethyl- 2.6-dinitroaniline. and

b. 2-(3.4-dichlorophenyl)-4-methyl-1,2.4-

oxadiaZolidine-3.S-dione in a weight ratio of ab in the range of 5:1 to 1:3.

4. A herbicide composition as claimed in claim 3 wherein compound (a) is N-propyl-N-B-chloroethyl-4- trifluoromethyl-Z,-dinitroaniline.

5. A herbicide composition as claimed in claim 3 wherein compound (a) is 4-trifluoromethyl-2,6-dinitro- N.N-dipropylaniline.

6. A process for controlling the growth of unwanted plants among crop plants wherein the soil in which the growth of unwanted plants among crop plants is to be prevented is treated with a herbicidally effective 5 amount of a mixture of a. a compound having the formula wherein R is trifluoromethyl and R'- is nitro. R is propyl or B-chloroethyl and R is propyl or ally], and

b. a compound selected from the group consisting of 2-(m-isopropylcarbamoyloxyphenyl)-4-methy1- 1,2,4-oxadiazo1idine-3 .5 -dione and 2-( 3 ,4- dichlorophenyl )-4-methy1- l ,2,4-oxadiazolidine- 3.5-dione in a weight ratio of azb in the range of 5:1 to 1:3.

7. A process as claimed in claim 6 wherein compound a is a member selected from the group consisting of 4-trifluoromethy1-2.o-dinitro-N.N-dipropylaniline. 4-trifluoromethyl-2.6-dinitro-N-B-chloroethyl-N- allylaniline and N-propyl-N-fi-chloroethy1-4- trifluoromethyl-Z,o-dinitroaniline.

8. A process for controlling the growth of unwanted plants among crop plants wherein the soil in which the growth of unwanted plants among crop plants is to be prevented is treated with a herbicidally effective amount of a mixture of the compounds a. 4-trifluoromethyl-2,6-dinitro-N,N-dipropylaniline or N-propyl-N-B-chloroethyl-4-trifluoromethyl- 2,6-dinitroani1ine and b. 2-( 3 .4-dichlorophenyl-4-methyl-1,2.4-

oxadiazo1idine-3.5-dione in a weight ratio of tub in the range of 5:1 to 1:3.

9. A process as claimed in claim 8 wherein compound '(a) is N-propyl-N-B-chloroethyl-4- trifluoromethyl-2,o-dinitroaniline.

10. A process as claimed in claim 8 wherein compound (a) is 4-trifluoromethyl-2,6-dinitro-N.N-

dipropylaniline. 

1. A HERBICIDE COMPOSITION CONTAINING A HERBICIDALLY EFFECTIVE AMOUNT OF A MIXTURE OF A. A COMPOUND HAVING THE FORMULA 1-(R3-N(-R4)-),2-R2,4-R1,6-(O2N-)BENZENE WHEREIN R1 IS TRIFLUOROMETHYL AND R2 IS NITRO, R3 IS PROPYL OR B-CHLOROETHYL AND R4 IS PROPYL OR ALLYL, AND B. A COMPOUND SELECTED FROM THE GROUP CONSISTING OF 2-(MISOPROPYLCARBAMOYLOXYPHENYL)-4-METHYL-1,2,4OXADIAZOLIDINE-3,5-DIONE AND 2-(3,4-DICHLOROPHENYL)-4METHYL-1,2,4-OXADIAZOLIDINE-3,5-DIONE IN A WEIGHT RATIO OF A:B IN THE RANGE OF 5:1 TO 1:3.
 2. A herbicide composition as claimed in claim 1 wherein compound a is a member selected from the group consisting of 4-trifluoromethyl-2,6-dinitro-N,N-dipropylaniline, 4-trifluoromethyl-2,6-dinitro-N- Beta -chloroethyl-N-allylaniline, and N-propyl-N- Beta -chloroethyl-4-trifluoromethyl-2,6-dinitroaniline.
 3. A herbicide composition containing a herbicidally effective amount of a mixture of the compounds a. 4-trifluoromethyl-2,6-dinitro-N,N-dipropylaniline or N-propyl-N- Beta -chloroethyl-4-trifluoromethyl-2,6-dinitroaniline, and b. 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione in a weight ratio of a:b in the range of 5:1 to 1:3.
 4. A herbicide composition as claimed in claim 3 wherein compound (a) is N-propyl-N- Beta -chloroethyl-4-trifluoromethyl-2,6-dinitroaniline.
 5. A herbicide composition as claimed in claim 3 wherein compound (a) is 4-trifluoromethyl-2,6-dinitro-N,N-dipropylaniline.
 6. A process for controlling the growth of unwanted plants among crop plants wherein the soil in which the growth of unwanted plants among crop plants is to be prevented is treated with a herbicidally effective amount of a mixture of a. a compound having the formula
 7. A process as claimed in claim 6 wherein compound a is a member selected from the group consisting of 4-trifluoromethyl-2,6-dinitro-N,N-dipropylaniline, 4-trifluoromethyl-2,6-dinitro-N- Beta -chloroethyl-N-allylaniline and N-propyl-N- Beta -chloroethyl-4-trifluoromethyl-2,6-dinitroaniline.
 8. A process for controlling the growth of unwanted plants among crop plants wherein the soil in which the growth of unwanted plants among crop plants is to be prevented is treated with a herbicidally effective amount of a mixture of the compounds a. 4-trifluoromethyl-2,6-dinitro-N,N-dipropylaniline or N-propyl-N- Beta -chloroethyl-4-trifluoromethyl-2,6-dinitroaniline and b. 2-(3,4-dichlorophenyl-4-methyl-1,2,4-oxadiazolidine-3,5-dione in a weight ratio of a:b in the range of 5:1 to 1:3.
 9. A process as claimed in claim 8 wherein compound (a) is N-propyl-N- Beta -chloroethyl-4-trifluoromethyl-2,6-dinitroaniline.
 10. A process as claimed in claim 8 wherein compound (a) is 4-trifluoromethyl-2,6-dinitro-N,N-dipropylaniline. 